Linear polyester compositions containing a 2,4,5-trihydroxy phenone of a fatty acid as a heat stabilizer



LINEAR POLYESTER COMPOSITIONS CONTAIN- ING A 2,4,5-TRIHYDROXY PHENONE OF A nite States Patent 2,856,383 Patented Oct. 14, .1958

We have found that linear polyesters can be heat stabilized by the incorporation of a small proportion of a 2,4,5-trihydroxyphenone of a fatty acid, having the formula FATTY ACID AS A HEAT STABILIZER 5 0 M B Knowles and Louis D. Moore, Jr., Kingsport, HO i JR Tenn., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey H No Drawing. Application September 24, 1956 Serial No. 611,782 In which R is an alkyl group of from 3 to 17 carbon atoms. 4 Claims The 2,4,5-trihydroxyphenone of a fatty acid can be incorporated into the resin either by mixing it into the Thisanvention relates to the heat stabilization of synmolten i hich may then be extruded or molded, them linear p y e 0f hlgh molecular Weight Linear or by adding it to a solution or dope of the resin, which polyesters are extenswely used in textile fibers, which are may h b Cast as a fil or Spun as a fil c sublebt t0 heatmg 111 tbeprbbesses 0f P y b at centrations of from 0.1 to 10 parts by weight of the elevated temperatures, roning and pressing. Llnear 2,4,5-t ihyd y henone of a fatty acid per 100 parts by p y f are also b 1111511115 and Shaped artlbles Whlch 20 weight of linear polyester may be used; we prefer to use are sub ected to heatlng in their various uses, such as f m 0.3 to 3 parts per 100 parts of polyester. in electrical 1nsulat10n and the like. Heating tends to de- Th effectiveness of h bili was tested b l grade 11I1eaf P y as has b dlscussbd y ing film strips of the polyester containing the stabilizer in Pohl in Journal of the American Chemical Society, a 200 C. ai oven for a given length of time. The 5660561 and y L Marshall and Todd values of {1 were determined before and after the heat- 111 Transactlobs of the Faraday y: 49, 6748 ing. A comparison of these figures with those obtained when p y b heated at blbvated temperatures, on a blank of the same batch of polyester provided a y degrade 1n p y l p pe s molecular measure of the stabilizing effect of the additive. Weight as measured y b logarltbmlc ylscoslty number, so In the examples given below, 2,4,5-trihydroxyphenones {17}, defined y the Bquatlon of fatty acids were incorporated in the indicated proporlnh/m) tions with a linear polyester designated as 5:1:6-S2A2P, ifl made from a 5:136 mole ratio of 4,4-dicarboxyphenyl sulfone, HOOCC H .SO .C H -COOH:succinic acid: where no and 7 are the viscositles respectively of pure 35 1,5-pentanediol, with a linear polyester designated as solvent and of a solution containing C grams of polymer 3:2:5-C:S:B, made from a 3:225 mole ratio of azelaic per 100 cc. of solvent. The logarithmic viscosity numbers acid:4,4'-dicarboxyphenyl sulfone: 1,4 butanediol, and reported herein were measured in a :40 mixture by with a linear polyester designated as 3:2:5-TzBzH, made weight of phenolztetrachloroethane at a polymer confrom a 3:2:5 mole ratio of terephthalic acidzsebacic acid: centratlon of about 0.23 gram/100 cc. 40 cyclohexane-1,4-dimethanol. Cyclohexane-1,4-dimethanol In the course of our investigation of the thermal breakhas the formula HO.CH .C H .CH .OH.

Examples Parts Stabilizer per 100 Parts Polyester Polyester Original After After 15 hrs. 63 hrs.

1 1of2,4,fi-trihydroxy-stearophenone- 6:1:6-S:A:P 0.69 0.70 one e 0- 70 0.34

1.03 0.97"... Insoluble. 1.11 Insoluble... Do. 3 1.00 0.99 Do. None S 1.11 Insoluble. Do. 4 lot 2,4,5-trihydroxy-stearophenone. 1.07 1,31 0.34. None 1.08 0.35m"... 0.12. 5 {1of2,4,5-trihydroxy-bntyrophenone .t 1.11 0.81 0.14. 1.08 0.35. 0.12.

down of linear polyesters, we have found that the addition of certain compounds to the polyesters retards thermal degradation. The mechanism of this protection is not completely understood, but it has been shown that oxygen has a detrimental effect; therefore, the compounds may be functioning as antioxidants. However, we have found that a great many antioxidants are not stabilizers for linear polyesters.

Insolubility of a sample after heating indicates that considerable degradation has taken place during the heatmg.

What we claim as our invention and desire to be secured by Letters Patent of the United States is:

l. A polyester composition comprising a linear polyester of a dihydric alcohol with two dicarboxylic acids, stabilized against degradation by heat by a content of 3 from 0.1 to 10 parts by weight of a 2,4,5-trihydroxyphenone of a fatty acid, having the formula Boats 0 Hogan on i in which R is an alkyl group of from 3 to 17 carbon atoms, per 100 parts by weight of polyester.

3. A polyester composition comprising a linear polyester of a dihydric alcohol with two dicar'boxyl'ic acids, stabilized against degradation by heat by a content of from 0.3 to 3 parts by weight of 2,4,5-trihydroxy-butyrophenone per parts by weight of polyester.

4. A polyester composition comprising a linear polyester of a dihydric alcohol with two dicarboxylic acids, stabilized against degradation by heat by a content of from 0.3 to 3 parts by weight of 2,4,5-trihydroxy-stearophenone per 100 parts by weight of polyester.

References Cited in the file of this patent UNITED STATES PATENTS 2,759,828 Bell et al. Aug. '21, 1956 FOREIGN PATENTS 401,018 Great Britain Nov. 9, 1933 1,110,532 France Feb. 14, 1956 OTHER REFERENCES Bergel: Chemistry and Industry, April 1, 1944, naaes 127' and 128. 

1. A POLYESTER COMPOSITION COMPRISING A LINEAR POLYESTER OF A DIHYDRIC ALCOHOL WITH TWO DICARBOXYLIC ACIDS, STABILIZED AGAINST DEGRADATION BY HEAT BY A CONTENT OF FROM 0.1 TO 10 PARTS BY WEIGHT OF A 2,4,5-TRIHYDROXYPHENONE OF A FATTY ACID, HAVING THE FORMULA 